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1. (Article ID: 2843)
Fischer W, Koch HU, Rösel P, Fiedler F
Alanine ester-containing native lipoteichoic acids do not act as lipoteichoic acid carrier. Isolation, structural and functional characterization
Journal of Biological Chemistry 255(10) (1980)
4557-4562
For the isolation of lipoteichoic acids from Gram- positive bacteria, a procedure has been worked out that avoids loss of alanine ester substituents. Operations were performed at pH 4 to 5 and, as far as possible, at 4°C. Lipoteichoic acids were isolated from Staphylococcus aureus, Lactobacillus helveticus, and Streptococcus lactis, and studied in terms of lipid anchor, chain length, and chain substitution. In the lipoteichoic acids from stationary phase cells of S. aureus and L. helveticus the glycerophosphate units were substituted with ester-bound D-alanine to an extent of 42 and 57%, respectively. During the logarithmic growth of S. aureus, substitution was between 51 and 54%. Stepwise hydrolysis of the lipoteichoic acid from S. aureus with phosphodiesterase and phosphomonoesterase from Aspergillus revealed a uniform distribution of the alanine ester substituents along the hydrophilic chain. Hydrolysis of the lipoteichoic acid from S. lactis with HF, and analysis of the water-soluble products revealed that approximately 39% of the glycerophosphate units carried α-D-galactosyl residues, 21% malanine ester, and 9% both of these substituents. None of these substituted lipoteichoic acids was used by the poly(ribitol phosphate) polymerase from S. aureus H as lipoteichoic acid carrier in contrast to their derivatives from which the substituents had been removed. These findings strongly suggest that lipoteichoic acids are physiologically incapable of functioning as lipoteichoic acid carrier in the biosynthesis of wall teichoic acids. The formation of lipoteichoic acid carrier * poly(ribito1 phosphate) complex in vitro observed earlier is now understood as an artifact since the ester-bound alanine of lipoteichoic acids is rapidly hydrolyzed at the pH (>7) used in these experiments.
NCBI PubMed ID: 7372593Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Institut für Physiologische Chemie der Universität Erlangen-Nürnberg, Erlangen, Germany, Lehrstuhl für Mikrobiologie der Universität München, Munich, Germany
The publication contains the following compound(s):
- Compound ID: 6306
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57%D-Ala-(1-2)-+ ?%LIP-(1-6)-+ LIP-(1-1)-+
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{{{-L-Gro-(1--P--3)--}}}/n=22/-L-Gro-(1--P--6)--b-D-Glcp-(1-6)-a-D-Galp-(1-2)-a-D-Glcp-(1-3)-L-Gro
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LIP-(1-2)-+ |
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Structure type: oligomer
Compound class: glycolipid
- Compound ID: 6307
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30%D-Ala-(1-2)-+ ?%LIP-(1-6)-+ LIP-(1-1)-+
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{{{-L-Gro-(1--P--3)--}}}/n=16-21/-L-Gro-(1--P--6)--b-D-Glcp-(1-2)-a-D-Glcp-(1-3)-L-Gro
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LIP-(1-2)-+ |
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Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
- Compound ID: 6308
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48%D-Ala-(1-2)-+ LIP-(1-1)-+
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{{{-L-Gro-(1--P--3)--}}}/n=18-20/-L-Gro-(1--P--6)--b-D-Glcp-(1-2)-a-D-Glcp-(1-3)-L-Gro
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LIP-(1-2)-+ |
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Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
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2. (Article ID: 3072)
Zubkov VA, Gorshkova RP, Ovodov YS
Structural studies of the O-specific polysaccharide chain of the Yersinia intermedia O:4,33 lipopolysaccharide
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14 (1988)
65-68
Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok
Methods: 13C NMR
The publication contains the following compound(s):
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3. (Article ID: 7792)
Sitrin RD, Chan G, Dingerdissen J, DeBrosse C, Mehta R, Roberts G, Rottschaefer S, Staiger D, Valenta J, Snader KM, Stedman RJ, Hoover JRE
Isolation and structure determination of Pachybasium cerebrosides which potentiate the antifungal activity of aculeacin
The Journal of Antibiotics 41(4) (1988)
469-480
A set of four cerebrosides was isolated from a Pachybasium species and purified by preparative reversed-phase HPLC. All four products displayed activity in a natural product screen aimed at detecting novel cell wall-active antifungal agents based on synergy with the known glucan synthetase inhibitor, aculeacin. Based on degradation studies, fast atom bombardment mass spectrometry and 13C and high field 1H NMR techniques, the structure of the major cerebroside was determined to be (4E,8E)-N-D-2'-hydroxy-(E)-3'-hexadecenoyl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadiene. The other components were found to be the corresponding 2'-hydroxypalmitic acid analog with one less double bond and an analogous pair containing 2'-hydroxystearic acid with and without the 3' double bond.
antifungal activity, Trichoderma, cerebroside, Pachybasium, aculeacin
NCBI PubMed ID: 3372353Publication DOI: 10.7164/antibiotics.41.469Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Institutions: Merck Sharp & Dohme Research Laboratories, West Point, USA, Consultant, Rohmand Haas, Philadelphia, USA, National Cancer Institute, Bethesda, USA, Temple University School of Pharmacy, Philadelphia, USA
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GC, biological assays, HPLC, extraction, reduction, CC, oxidation, melting point determination, COSY, hydrogenation
The publication contains the following compound(s):
- Compound ID: 19744
Structure type: monomer
; 726 [M+H]+
C41H75NO9
Compound class: cerebroside
- Compound ID: 19745
Structure type: monomer
; 728 [M+H]+
C41H77NO9
Compound class: cerebroside
- Compound ID: 19746
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b-D-Glcp-(1-1)-9b1SphdC19-(2-1)-Subst
Subst = 2R-hydroxyoctadec-3E-enoic acid = SMILES CCCCCCCCCCCCCC/C=C/{2}[C@@H](O){1}C(=O)O |
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Structure type: monomer
; 754 [M+H]+
C43H79NO9
Compound class: cerebroside
- Compound ID: 19747
Structure type: monomer
; 756 [M+H]+
C43H81NO9
Compound class: cerebroside
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4. (Article ID: 7852)
Tan QW, Ouyang MA, Shen S, Li W
Bioactive metabolites from a marine-derived strain of the fungus Neosartorya fischeri
Natural Product Research 26(15) (2012)
1402-1407
Two new compounds named fischeacid and fischexanthone, together with eight known compounds, were obtained from the culture of a marine-derived fungus Neosartorya fischeri strain 1008F1. The structures of the new compounds were elucidated based on the spectroscopic data. Bioassays indicated that AGI-B4 and 3,4-dihydroxybenzoic acid showed potent inhibitory effect on the replication of tobacco mosaic virus, and AGI-B4 also possessed an inhibition of the cell proliferation of human gastric cancer cell line SGC-7901 and hepatic cancer cells BEL-7404.
cytotoxicity, Neosartorya fischeri, fischeacid, fischexanthone, antiphytoviral effect
NCBI PubMed ID: 21916772Publication DOI: 10.1080/14786419.2011.592834Journal NLM ID: 101167924Publisher: Milton Park, UK : Taylor & Francis Health Sciences
Correspondence: maouyang

hqu.edu.cn
Institutions: Institute of Plant Virology, Fujian Agriculture and Forestry University, Fuzhou, China, Institute of Biotechnology, Qinghai Academy of Agriculture and Forestry, Xining, China
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, UV, extraction, gel chromatography, optical rotation measurement, CC, cell growth
The publication contains the following compound(s):
- Compound ID: 19877
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b-D-Sug5Me-(1-9)-Subst
Sug = 5-amino-5-deoxy-D-ribofuranose = SMILES O{5}C[C@H]1O{1}[C@@H](O)[C@H](O)[C@@H]1O;
Subst = adenine = SMILES Nc1ncnc2{9}[nH]cnc12 |
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Structure type: monomer
Trivial name: 5'-deoxy-5'-methylamino-adenosine
Compound class: glycoside
Reference(s) to other database(s): GenDB: EU926976
- Compound ID: 19878
Structure type: monomer
Trivial name: adenosine, Adenosine
Compound class: glycoside, flavonoid glycoside, nucleoside
Reference(s) to other database(s): GenDB: EU926976
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